Guilford vacation rentals

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Top-rated vacation rentals in Guilford

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Guilford

4.96 out of 5 average rating, 157 reviews

Luxury cottage by the sea with hot tub and pool

We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

Jan 12 – 19

R6,364 ZAR per night

Guest favorite

Cottage in Guilford

4.93 out of 5 average rating, 244 reviews

Charm + location. Walk to beach, town, & harbor.

We are sharing our "happy place". Cozy, family-friendly cottage has everything you need to enjoy a lovely vacation in a quintessential New England town. Ideally located between Guilford's famous green, gorgeous harbor and town beach, easily walk everywhere. High-season/weekend rate reflected in general view--check for actual. Recommended for groups of up to 4 (5 if with kids). Second bedroom (king) is open to living area-we provide a folding screen for door area and curtain for “passthrough”.

Feb 10 – 17

R5,426 ZAR per night

Guest favorite

Apartment in Chester

4.95 out of 5 average rating, 313 reviews

Chester Village 'Pied-à-terre' above art gallery

If finding a place in an ideal location w/ thoughtful design matters to you, then you've found it! Sunshine filled living room w/ high ceilings, a private bedroom in back w/ large private deck overlooking Pattaconk Brook. Our place is a gem, and set up for the comfort of our guests. Located in the heart of Chester Village, above our art gallery & boutique, and neighbor to some of the BEST restaurants, art and shopping in CT! NEW! Winter weekdays - ONE night stays are now available - message us!

Nov 13 – 20

R3,805 ZAR per night

Guest favorite

Apartment in Guilford

4.98 out of 5 average rating, 248 reviews

Guilford Guest House- private studio apartment

Quintessential New England shoreline town. Arrive by Car, Train or by boat and walk from the marina to our guest house. (Inquire) Walk to the Guilford Green, Town Dock, Jacobs Beach along with over a dozen restaurants, pubs, coffee shops, gift & clothing shops. Hiking trails . Please review my extensive guide book of Guilford and the surrounding areas. Walking access to the Shoreline East train to surrounding Local towns or transfer to Metro north and Amtrak to NYC & Boston all without a car.

Jan 22 – 29

R3,013 ZAR per night

Guest favorite

Guest suite in Wallingford

5.0 out of 5 average rating, 496 reviews

Wintergreen Gardens Suite @ William Becroft House

LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, pvt. entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station. Coming for a special event? Book an appointment at our salon, Jimmy James Salon. Ask for info.

Aug 12 – 19

R1,659 ZAR per night

Guest favorite

Yurt in Guilford

4.9 out of 5 average rating, 100 reviews

Hartwoods Yurt

Enjoy a unique, private, wilderness getaway and unwind in a peaceful wooded environment in our 30’ diameter Yurt, which sleeps 4 in North Guilford, CT. This elevated cylindrical dwelling offers solitude and a large deck with comfortable chairs and forest views. Shaded and cool in the summer with air conditioning and fans available. This Yurt provides a wonderful respite from the hectic world. Perfect for nature lovers with a nearby brook and miles of trails for hiking and mountain biking.

Feb 16 – 23

R4,051 ZAR per night

Guest favorite

Apartment in Guilford

4.9 out of 5 average rating, 20 reviews

Cozy Private Lake Q Retreat

Escape to a charming lakeside haven! Our cozy 1-bed, 1-bath retreat is a tranquil getaway. Nestled by the water, it's perfect for a romantic escape or a solo recharge. Enjoy stunning lake views, a comfy bedroom, and a serene bathroom. Unwind on the private deck, take a dip in the crystal-clear waters, or explore nearby nature trails. A lofted office space with l-shaped desk and computer monitor with connection hub invites both creativity and productivity. Your lakeside escape awaits!

Mar 26 – Apr 2

R2,909 ZAR per night

Guest favorite

Tiny home in Guilford

4.94 out of 5 average rating, 202 reviews

Stay in a Tiny House on a Small Sustainable Farm

Come stay in a tiny house on our sustainable farm! Tucked behind an unassuming neighborhood, feel your cares drop away as you drive down the long gravel driveway and our bucolic 8 acres open in front of you. We have goats, ducks and chickens. Hike, swim, kayak, play with goats, have a picnic or just plain relax. There are so many possibilities. The tiny house has AC/heat, wifi, full kitchen, full bath and a queen sized bed in the loft. Get away from it all here at Waystone Farm.

Aug 23 – 30

R3,291 ZAR per night

Guest favorite

Apartment in Middletown

4.98 out of 5 average rating, 147 reviews

Apartment Near Wesleyan, Downtown, Wedding Venues!

Welcome! We are sure you will enjoy your stay in this centrally located first-floor apartment, which sleeps 5-6 guests! You'll feel at home in this cozy 2-bedroom unit, stocked with everything you would need during your stay. Walking distance away from Main Street and Wesleyan, you'll be able to explore all Middletown and the surrounding area has to offer. Two porches, a fenced-in backyard, and a firepit are all available for your use! Pets are welcome! Any questions? Message us!

Sep 4 – 11

R2,457 ZAR per night

Guest favorite

Apartment in East Haddam

4.9 out of 5 average rating, 105 reviews

Penny Corner Airbnb

My place is located up the hill from Good Speed Opera House. The Opera House is on the same side of the river as my place. The folklore is that vacationers used to pay a penny to have their belongings transported by ox and wagon from the port at the river to this corner. A two family home built in 1884. The space is a ground level 1 bedroom apartment with private entrance. There is no TV in the unit, WIFI is available for your devices.

Jan 16 – 23

R1,952 ZAR per night

Guest favorite

Home in Guilford

4.95 out of 5 average rating, 19 reviews

Tiny home one block from the town green.

This special place is close to everything, The town green is one street over with local shops and restaurants. Walking distance to the train station, town marina, and the Guilford beach. It's a small home suitable for 2 people at the most. The bathroom is very small with a very small sink but a full size shower. AC/heat, wifi, full kitchen, shower, full size bed in a quiet private setting.

Sep 30 – Oct 7

R2,827 ZAR per night

Guest favorite

Guesthouse in Guilford

4.99 out of 5 average rating, 453 reviews

Get Back to Nature at a Modern Wood Clad Getaway

SPRING BIRDS HAVE ARRIVED. Spring is here!!. Beautiful days and nights. Hike on the trails. Bike along the ocean. Cardinals, blue jays, bluebirds, gold finches and more. Great places to shop and eat or just relax in our cozy guest house. Enjoy! We want you to have a relaxing stay with us, free from worry. We are located in a private area, away from public.

Nov 11 – 18

R5,438 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Guilford vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Guilford's top sights

Jacobs Beach17 locals recommend

The Place Restaurant31 locals recommend

Shoreline Diner & Vegetarian Enclave12 locals recommend

Bishop's Orchards Farm Market & Winery57 locals recommend

Guilford Town Green22 locals recommend

Guilford Mooring18 locals recommend

Other great vacation rentals in Guilford

Guest favorite

Guest suite in Guilford

4.93 out of 5 average rating, 75 reviews

Old Salt Oasis: serene, spacious, pets welcome!

Jun 24 – Jul 1

R3,599 ZAR per night

Guest favorite

Home in Guilford

4.89 out of 5 average rating, 37 reviews

Guilford cozy in-law apt with private entrance

Jul 9 – 16

R2,947 ZAR per night

Guest favorite

Guest suite in Guilford

4.93 out of 5 average rating, 29 reviews

Guilford studio apartment, steps from the Green

Oct 4 – 11

R3,351 ZAR per night

Guest favorite

Guesthouse in Guilford

5.0 out of 5 average rating, 61 reviews

Page Guest House

Nov 19 – 26

R4,766 ZAR per night

Superhost

Apartment in Branford

4.89 out of 5 average rating, 9 reviews

Stony Crk Studio ideal for trvl nurses…

Jan 4 – 11

R1,872 ZAR per night

Guest favorite

Vacation home in Guilford

4.98 out of 5 average rating, 60 reviews

Spacious Oceanfront Getaway with Spectacular Views

Dec 12 – 19

R10,915 ZAR per night

Guest favorite

Guest suite in Northford

5.0 out of 5 average rating, 12 reviews

Private Bright Studio Retreat with kitchen

Aug 8 – 15

R1,698 ZAR per night

Guest favorite

Tiny home in Guilford

4.95 out of 5 average rating, 44 reviews

Seagrass Bungalow

Aug 11 – 18

R5,517 ZAR per night

Show all

Other great vacation rentals in Guilford

Guest favorite

Home in Guilford

5.0 out of 5 average rating, 46 reviews

Field of Dreams Hot Tub - Fire Pit Retreat

Aug 7 – 14

R14,197 ZAR per night

Guest favorite

Cottage in Guilford

5.0 out of 5 average rating, 81 reviews

Waterfront Joshua Cove Cottage with private beach.

Dec 2 – 9

R7,933 ZAR per night

Guest favorite

Apartment in Guilford

5.0 out of 5 average rating, 28 reviews

The Leete House a taste of Historic Guilford

Jul 20 – 27

R5,480 ZAR per night

Guest favorite

Guesthouse in Guilford

4.99 out of 5 average rating, 76 reviews

Guilford Lakes Cottage, with hot tub and fire pit.

Jun 24 – Jul 1

R5,581 ZAR per night

Guest favorite

Guest suite in Durham

4.84 out of 5 average rating, 19 reviews

Spacious Studio in quiet neighborhood.

Jun 30 – Jul 7

R2,079 ZAR per night

Superhost

Guesthouse in Guilford

4.84 out of 5 average rating, 38 reviews

Charming Bungalow walk to beach and town

Oct 4 – 11

R1,878 ZAR per night

Guest favorite

Guesthouse in Madison

4.92 out of 5 average rating, 13 reviews

In-law apartment with Private entrance

Oct 23 – 30

R2,316 ZAR per night

Guest favorite

Apartment in Clinton

4.98 out of 5 average rating, 49 reviews

Cozy Shoreline Getaway

Mar 28 – Apr 4

R2,469 ZAR per night

Show all

Quick stats about vacation rentals in Guilford

Total rentals
100 properties
Wifi availability
100 properties include access to wifi
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
5.4K reviews

Frequently Asked Questions

Are there pet-friendly vacation rentals in Guilford?
Four-legged friends are welcome in Guilford. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Guilford?
Yes! Work meets play with ease at over 60 vacation rentals in Guilford featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do cottage rentals in Guilford have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Guilford. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in cottage rentals in Guilford?
Experience the best of Guilford with our cottage rentals, starting at about $130 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly house rentals in Guilford?
Guilford has more than 40 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Guilford have air conditioning?
Absolutely! We offer over 50 house rentals with air conditioning in Guilford. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Guilford have a bbq area?
Absolutely! We offer over 30 house rentals with a bbq area in Guilford. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Cottage Rentals in Guilford?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 10 homes with a bbq area, over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Guilford vacation rentals

Top-rated vacation rentals in Guilford

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Guilford vacation rentals

Stay near Guilford's top sights

Other great vacation rentals in Guilford

Guest suite in Guilford

Home in Guilford

Guest suite in Guilford

Guesthouse in Guilford

Apartment in Branford

Vacation home in Guilford

Guest suite in Northford

Tiny home in Guilford

Other great vacation rentals in Guilford

Home in Guilford

Cottage in Guilford

Apartment in Guilford

Guesthouse in Guilford

Guest suite in Durham

Guesthouse in Guilford

Guesthouse in Madison

Apartment in Clinton

Quick stats about vacation rentals in Guilford

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Are there pet-friendly vacation rentals in Guilford?

Are there vacation rentals with a dedicated workspace in Guilford?

Do cottage rentals in Guilford have wifi?

How much does it cost to stay in cottage rentals in Guilford?

Are there family-friendly house rentals in Guilford?

Do house rentals in Guilford have air conditioning?

Do house rentals in Guilford have a bbq area?

What are the most popular amenities for Cottage Rentals in Guilford?

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